A challenge to Baldwin's role: Development of the unified methodology for controlling the cyclization mode
| Project/Area Number |
15K07878
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kobe Pharmaceutical University |
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Principal Investigator |
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| Project Period (FY) |
2015-04-01 – 2018-03-31
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| Project Status |
Completed (Fiscal Year 2017)
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| Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | 環化反応 / ヨウ素 / アルキン / イナミド / β-シリル効果 / Baldwin則 / 環化様式 / 配向基 / β－シリル効果 |
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| Outline of Final Research Achievements |
In the iodocyclization, the regioselectivity of nucleophilic position toward alkynes has established as Baldwin’s role. Therefore, the control of the cyclization mode is difficult when both endo- and exo-mode are favored. I have developed the unified methodology for controlling the iodocyclization mode of alkynes by using directing groups.
Amide-substituted alkynes, namely ynamides, were suitable for endo-selective iodocyclizations. In contrast, the iodocyclization of alkynes proceeded in exo mode when silyl groups were used as directing groups. During the course of this project, I serendipitously found that 3-methylene-4-amido-1,2-diazetidine was prepared for the first time via formal [2+2] cycloaddition of an allenamide and an azo compound. This worked as a formal 1,4-dipole precursor toward nucleophilic addition with various silyl nucleophiles.
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Report
(4 results)
Research Products
(35 results)
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[Presentation] Preparation of New ChR with One Double Bond-elongated 3,4-Dehydroretinals2015
Author(s)
Wada, A.; Okitsu, T.; Yamano, Y.; Kobayashi, Y.; Ishizuka, T.; Yawo, H.; Matsuyama, T.; Yamashiya, T.; Imamoto, Y.; Shichida, Y.
Organizer
The 3rd International Conference on Retinoids
Place of Presentation
Gifu
Year and Date
2015-10-21
Related Report
Int'l Joint Research
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